Issue 18, 2009
From the journal:

Organic & Biomolecular Chemistry

Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides†

Hou-Hua Lia  and  Xin-Shan Ye*a  

* Corresponding authors

a State Key Laboratory of Natural and Biomimetic Drugs, Peking University, and School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing, China
E-mail: xinshan@bjmu.edu.cn
Fax: +86-10-62014949
Tel: +86-10-62014949

Abstract

The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)2 to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag2CO3 and Cu(OAc)2 (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.

Graphical abstract: Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides

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Article information

DOI
https://doi.org/10.1039/B909248J
Article type
Paper
Submitted
11 May 2009
Accepted
22 Jun 2009
First published
20 Jul 2009

Org. Biomol. Chem., 2009,7, 3855-3861

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Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides

H. Li and X. Ye, Org. Biomol. Chem., 2009, 7, 3855 DOI: 10.1039/B909248J

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